Wattaquadock Hill is a 640-foot ridge in southwest Bolton, Massachusetts, the town’s highest point and a landscape combining natural features with early regional history. Its protected conservation land preserves woods, streams, a pond, wetlands, and the foundation of an observation tower, though the true summit is on private land. The hill’s Indigenous name has uncertain meaning and has appeared in many spellings since the seventeenth century. It was in local records by 1655, crossed by an Indigenous trail used by trader Thomas King in 1642, and associated with conflict during King Philip’s War. Farming by the Wheeler and Howe families continued along the ridge for nearly 270 years.